Walt Disney originally purchased the rights to the Winnie the Pooh stories in the mid-1960s. Since he was a bit concerned about the interest in this character in the U.S. (Pooh was primarily known in Britain), he decided to make a test film as a theatrical featurette. It would be the right length to also be sold as a half-hour television show. That first Disney Pooh featurette was Winnie the Pooh and the Honey Tree (1966), directed by Disney veteran Wolfgang Reitherman and featuring catchy songs by Robert B. and Richard M. Sherman. Sterling Holloway was perfectly cast as the voice of Pooh, and the film was narrated by Sebastian Cabot.

Paired on a double bill with The Ugly Dachsund, the Pooh film was a big hit in itself, and soon was followed by theatrical sequels Winnie the Pooh and the Blustery Day (1968) and Winnie the Pooh and Tigger Too (1974). The first three Pooh featurettes were combined, in 1977, into a feature-length The Many Adventures of Winnie the Pooh. Interest in the new character from the Disney films was initially aided by a comprehensive marketing agreement with Sears.

Other Pooh films followed, such as Winnie the Pooh and a Day for Eeyore (for theaters, 1983), Winnie the Pooh Discovers the Seasons, Winnie the Pooh's ABC of Me (for schools, 1981 and 1990), Winnie the Pooh and Christmas Too and Winnie the Pooh: a Valentine for You (for television, 1991 and 1999). At Disneyland park, there were popular Winnie the Pooh for President days in 1972 and 1976. The Tigger Movie, featuring six new songs by the Sherman Brothers, bounced into theaters in 2000.

With the growing popularity of Winnie the Pooh merchandise, The Walt Disney Company decided in 2001 to purchase the complete merchandising rights to the character. Today, Winnie the Pooh is second only to Mickey Mouse as the favorite Disney character.